(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S)-5-[(E)-3-hydroxyprop-1-enyl]-7-methoxy-2-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydro-1-benzofuran-3-yl]methoxy]oxane-3,4,5-triol

Details

• Internal ID: 5d82c937-c4b9-4805-800c-f62fdb095869
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S)-5-[(E)-3-hydroxyprop-1-enyl]-7-methoxy-2-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydro-1-benzofuran-3-yl]methoxy]oxane-3,4,5-triol
• SMILES (Canonical): COC1=CC(=CC2=C1OC(C2COC3C(C(C(C(O3)CO)O)O)O)C4=CC(=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)OC)C=CCO
• SMILES (Isomeric): COC1=CC(=CC2=C1O[C@H]([C@@H]2CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C4=CC(=C(C=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)OC)/C=C/CO
• InChI: InChI=1S/C32H42O16/c1-42-19-10-15(5-6-18(19)45-32-28(41)26(39)24(37)22(12-35)47-32)29-17(13-44-31-27(40)25(38)23(36)21(11-34)46-31)16-8-14(4-3-7-33)9-20(43-2)30(16)48-29/h3-6,8-10,17,21-29,31-41H,7,11-13H2,1-2H3/b4-3+/t17-,21-,22-,23-,24-,25+,26+,27-,28-,29+,31-,32-/m1/s1
• InChI Key: SLTFRIVPWOFMPR-PCUKYLCZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₂O₁₆
• Molecular Weight: 682.70 g/mol
• Exact Mass: 682.24728525 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.08
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5971	59.71%
Caco-2	-	0.8849	88.49%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6141	61.41%
OATP2B1 inhibitior	-	0.8638	86.38%
OATP1B1 inhibitior	+	0.8220	82.20%
OATP1B3 inhibitior	+	0.9744	97.44%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8449	84.49%
P-glycoprotein inhibitior	-	0.4594	45.94%
P-glycoprotein substrate	-	0.6807	68.07%
CYP3A4 substrate	+	0.6392	63.92%
CYP2C9 substrate	-	0.6243	62.43%
CYP2D6 substrate	-	0.7977	79.77%
CYP3A4 inhibition	-	0.8418	84.18%
CYP2C9 inhibition	-	0.8087	80.87%
CYP2C19 inhibition	-	0.7157	71.57%
CYP2D6 inhibition	-	0.8635	86.35%
CYP1A2 inhibition	-	0.8855	88.55%
CYP2C8 inhibition	+	0.7387	73.87%
CYP inhibitory promiscuity	+	0.6891	68.91%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5372	53.72%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9304	93.04%
Skin irritation	-	0.8307	83.07%
Skin corrosion	-	0.9485	94.85%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8514	85.14%
Micronuclear	+	0.6759	67.59%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8531	85.31%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6928	69.28%
Acute Oral Toxicity (c)	III	0.6909	69.09%
Estrogen receptor binding	+	0.8138	81.38%
Androgen receptor binding	+	0.5499	54.99%
Thyroid receptor binding	+	0.5497	54.97%
Glucocorticoid receptor binding	-	0.4663	46.63%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6487	64.87%
Honey bee toxicity	-	0.7665	76.65%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.8550	85.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.23%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.06%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.37%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.62%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.83%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	91.39%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.81%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.90%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.93%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.61%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.85%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.98%	89.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.63%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.59%	95.89%
CHEMBL2581	P07339	Cathepsin D	80.59%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	80.28%	91.49%

Plants that contains it

• Verbascum thapsus

Cross-Links

• PubChem: 15736506
• LOTUS: LTS0251855
• wikiData: Q105255626